• Media type: E-Article
  • Title: Toward the Synthesis of Tetrazino‐­tetrazine 1,3,6,8‐Tetraoxide (TTTO): An Approach to Non‐annulated 1,2,3,4‐Tetrazine 1,3‐Dioxides
  • Contributor: Klenov, Michael S.; Anikin, Oleg V.; Churakov, Aleksandr M.; Strelenko, Yurii A.; Fedyanin, Ivan V.; Ananyev, Ivan V.; Tartakovsky, Vladimir A.
  • Published: Wiley, 2015
  • Published in: European Journal of Organic Chemistry, 2015 (2015) 28, Seite 6170-6179
  • Language: English
  • DOI: 10.1002/ejoc.201500923
  • ISSN: 1434-193X; 1099-0690
  • Origination:
  • Footnote:
  • Description: AbstractA novel approach for the synthesis of 6‐(tert‐butyl‐NNO‐azoxy)‐5‐methylthio‐1,2,3,4‐tetrazine 1,3‐dioxide (1) was developed. This compound is likely to be a precursor of tetrazino‐tetrazine 1,3,6,8‐tetraoxide. The synthetic strategy consists of four steps: a synthesis of bis(tert‐butyl‐NNO‐azoxy)methane, coupling of the latter with dimethyl nitrodithioimidocarbonate to give N‐nitroimine 3, O‐alkylation of the latter to O‐alkylated nitroenamine and its reaction with BF3·Et2O to afford tetrazine 1,3‐dioxide 1. An X‐ray diffraction study of 1 was accomplished.